Ethane → HCID 3270829, compound

HRID 2309847

Reaction equation

HRID 2309847 reaction equation
CC.[CH2:3]=[CH:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]1[CH:23]=[C:22]([OH:24])[CH:21]=[CH:20][CH:19]=1.[CH:25]([O-])([O-])[O:26]CC>>[CH2:17]([C:18]1[CH:23]=[C:22]([OH:24])[C:21](=[CH:20][CH:19]=1)[CH:25]=[O:26])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH3:3]

Participants

4

Reactant 3

HCID 6324EthaneHCID 11266523CardanolHCID 53630039Ethylorthoformate

Product 1

HCID 3270829HCID 3270829, compound

Procedure

(15:0)-Cardanol (10.2 g) is added to an equivalent proportion of ethyl magnesium bromide in dry ethereal solution to form the phenoxy magnesium bromide, completion of which is observed when evolution of ethane ceases. Ethyl orthoformate (10 cm3) is added and the ether removed by distillation so that the temperature rises to 100° C. After refluxing for three hours, the mixture is decomposed with dilute hydrochloric acid and warmed to effect the hydrolysis of the intermediate acetal formed. Etheral extraction and recovery gives a mixture of some unchanged (15:0)-cardanol and the formylated product, 4-pentadecylsalicylaldehyde which is separated by chromatography.

Workup

  1. customthe ether removed by distillation so that the temperature
  2. customrises to 100° C
  3. temperatureAfter refluxing for three hours
  4. temperaturewarmed
  5. customthe hydrolysis of the intermediate acetal
  6. customformed
  7. extractionEtheral extraction and recovery
  8. customgives
  9. customthe formylated product, 4-pentadecylsalicylaldehyde which is separated by chromatography

Sources & evidence

ORD record
ord-6be94184385c40ce923d9b2d1a9b99b1
Source dataset
uspto-grants-1987_09
Patent number
US04697038

Linked notes

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