Hydrochloric Acid → Ethyl 7-(4-hydroxyphenyl)heptanoate

HRID 36129Notes

Reaction equation

HRID 36129 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:4][CH:3]=1.Cl.C(=O)(O)[O-].[Na+].[CH2:23](O)[CH3:24]>>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:23][CH3:24])=[O:15])=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 516892Sodium BicarbonateHCID 148220177-(4-Hydroxyphenyl)heptanoic acid

Product 1

HCID 19940090Ethyl 7-(4-hydroxyphenyl)heptanoate

Procedure

A 500 ml single-neck flask was charged with 7-(4-hydroxyphenyl)heptanoic acid (A4) (17.7 g, 79.7 mmole), 35 ml of the 25% HCl solution, and ethanol (90 ml). The flask was immersed in an oil bath and refluxed 4.5 hours. After cooling to room temperature, the contents were poured onto ice water (750 ml) and 375 ml of saturated sodium bicarbonate were added. The mixture was extracted with ether (3×225 ml), the combined organic layers dried (MgSO4), and concentrated by rotary evaporation (2-4 hours at 45° C.). The resulting oil, Ethyl 7-(4-hydroxyphenyl)heptanoate, was of sufficient purity to be used in the next step.

Workup

  1. customThe flask was immersed in an oil bath
  2. temperaturerefluxed 4.5 hours
  3. additionwere added
  4. extractionThe mixture was extracted with ether (3×225 ml)
  5. dry with materialthe combined organic layers dried (MgSO4)
  6. concentrationconcentrated by rotary evaporation (2-4 hours at 45° C.)

Sources & evidence

ORD record
ord-d3868e1ba0604f259e5862921413dc4f
Source dataset
uspto-grants-1995_05
Patent number
US05412144

Reaction notes

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