Water → HCID 4681831, compound

HRID 1464627Notes

Reaction equation

HRID 1464627 reaction equation
[OH:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].[CH:12]1([CH3:22])[CH2:17][CH2:16][CH:15]([CH:18]([CH3:20])[CH3:19])[CH:14](O)[CH2:13]1.C1(C)C(S(O)(=O)=O)=CC=CC=1.O>C1(C)C=CC=CC=1>[OH:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([O:5][CH:14]1[CH:15]([CH:18]([CH3:20])[CH3:19])[CH2:16][CH2:17][CH:12]([CH3:22])[CH2:13]1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 1254MentholHCID 1292Mandelic AcidHCID 69252-Methylbenzenesulfonic acid

Product 1

HCID 4681831HCID 4681831, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2.1 kg of hydroxyphenylacetic acid are esterified with 2.5 kg of (-)-menthol in 15 l of boiling toluene with the addition of 40 g of toluenesulphonic acid; the water of reaction is removed from circulation in a water separator. When water is no longer separated, the mixture is cooled, washed with 4 l of saturated NaHCO3 and twice with 4 l of water and concentrated to dryness in vacuo. The title compound is obtained as an oily residue.

Workup

  1. customis removed from circulation in a water separator
  2. customWhen water is no longer separated
  3. temperaturethe mixture is cooled
  4. washwashed with 4 l of saturated NaHCO3 and twice with 4 l of water
  5. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-0db1e6c1022440e582805e72a56cfe31
Source dataset
uspto-grants-1994_04
Patent number
US05306820

Reaction notes

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